5α-Androst-16-en-3-on
Androstenone
Grundinformationen
- CAS
18339-16-7- Standard-SMILES
C[C@]12CCC(=O)C[C@@H]1CC[C@@H]1[C@@H]2CC[C@]2(C)C=CC[C@@H]12- InChIKey
HFVMLYAGWXSTQI-QYXZOKGRSA-N- Summenformel
- C19H28O
- Durchschnittliche Molmasse
- 272,4 g/mol
- Monoisotopische Masse
- 272,21401552
Überblick
5alpha-androst-16-en-3-one is an androstanoid that is 5alpha-androst-16-ene substituted by an oxo group at position 3. It is a steroid pheromone found in high concentrations in the saliva of male pigs,. It has a role as a pheromone and a mammalian metabolite. It is a 3-oxo steroid and an androstanoid. It derives from a hydride of a 5alpha-androst-16-ene.
Namen und Bezeichner
- Bevorzugter Name
- Androstenone
- IUPAC
- (5S,8R,9S,10S,13R,14S)-10,13-dimethyl-1,2,4,5,6,7,8,9,11,12,14,15-dodecahydrocyclopenta[a]phenanthren-3-one
- Lokaler Name
- 5α-Androst-16-en-3-on
- Englischer Name
- 5alpha-Androst-16-en-3-one
- Summenformel
- C19H28O
- Molmasse
- 272.42
Namen und Synonyme
androstenone18339-16-75alpha-Androst-16-en-3-oneAndrost-16-en-3-oneDTXSID0040965BWD3D5941JDTXCID8020965CHEBI:37894AEON steroidRefChem:558034DTXCID20209694DTXSID80860220
Weitere Namen anzeigen
OCCLESTERONEOxstersterone5α-AndrostenoneEinecs 242-220-116-(5α)androsten-3-one5Androstan-16-en-3-one5A-ANDROST-16-EN-3-ONE
242-220-15alpha-Androstenone5a-androstenone(5S,8R,9S,10S,13R,14S)-10,13-dimethyl-1,2,4,5,6,7,8,9,11,12,14,15-dodecahydrocyclopenta[a]phenanthren-3-one5|A-AndrostenoneAndrost-16-en-3-one, (5alpha)-MFCD00010479MLS000069748
Datenbank-Bezeichner
- CAS
18339-16-7- PubChem CID
- 6852393
- DTXSID
DTXSID0040965
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 4,9
- Polarare Oberfläche (TPSA)
- 17,1 Ų
- H-Brücken-Donoren
- 0
- H-Brücken-Akzeptoren
- 1
- Frei drehbare Bindungen
- 0
- Schwere Atome
- 20
- Formalladung
- 0
- Komplexität
- 464
Experimentelle und physikochemische Eigenschaften
LipidsLipids -> Sterol Lipids [ST] -> Steroids [ST02] -> C19 steroids (androgens) and derivatives [ST0202]
Boiling Point371.00 to 372.00 °C. @ 760.00 mm Hg
Melting Point140 - 141 °C
Physical DescriptionSolid
Physikochemische Eigenschaften
- Schmelzpunkt
- 140 · 140-145 °C(lit.)
- Siedepunkt
- 371.6 · 371.6±42.0 °C(Predicted)
- Dichte
- 1.032 · 1.032±0.06 g/cm3(Predicted)
- storage temp.
- 2 · 2-8°C
- Löslichkeit
- Chloroform (Slightly), Methanol (Slightly, Heated)
- Aggregatzustand
- Solid
- Farbe
- White to Off-White
- Biologische Quelle
- synthetic (organic)
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
GHS-Klassifizierung
GHS Classification
Danger
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
P203, P261, P264, P270, P271, P280, P301+P317, P302+P352, P304+P340, P317, P318, P321, P330, P362+P364, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 17 reports by companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Gefahrenhinweise
Other Safety InformationIMAP assessments - Androst-16-en-3-one, (5.alpha.)-: Human health tier I assessment
Hazard Classes and CategoriesAcute Tox. 4 (100%)
Sicherheitsdaten
- wgk
- -
- Speicherklasse
- 11 - Combustible Solids
Chemie und Industrie
Pharmakologische Informationen
Cellular LocationsExtracellular
Anwendungen
Verwenden5α-Androst-16-en-3-one is a mammalian pheromone released as a volatile chemical cue in boar saliva to facilitate social and sexual interactions. It has been used to prime sexual behavior of sows in estrus for mating or artificial insemination. 5α-androst-16-en-3-one is also found in human sweat and urine and has been used to study receptor-mediated odorant detection and the genetic basis for anosmias.
Vor- und nachgelagerte Produkte
Vorgelagerte Rohstoffe
Ergänzende Hinweise
DefinitionChEBI: 5alpha-androst-16-en-3-one is an androstanoid that is 5alpha-androst-16-ene substituted by an oxo group at position 3. It is a steroid pheromone found in high concentrations in the saliva of male pigs,. It has a role as a pheromone and a mammalian metabolite. It is a 3-oxo steroid and an androstanoid. It derives from a hydride of a 5alpha-androst-16-ene.
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